


The Great Panty-Off

by jhoom



Category: Supernatural
Genre: 69 (Sex Position), Blowjobs, College!AU, Gay Chicken, M/M, Multi, Rimming, Roommates, Threesome, Twincest, benny (mentioned) - Freeform, panty!kink
Language: English
Status: Completed
Published: 2016-11-22
Updated: 2016-11-22
Packaged: 2018-09-01 13:31:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,323
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8626360
Author URL: https://archiveofourown.org/users/jhoom/pseuds/jhoom
Summary: Where Dean, Cas, and Jimmy play a dangerous game of gay chicken by making a bet on who can wear panties the longest.





	

**Author's Note:**

> So this fic was written for the November [Rare Ship Creations Challenge](http://rareshipcreationschallenge.tumblr.com). My nsfw prompt was 'panties' and I am very very happy to play around with dcj in panties ;)
> 
> Come visit me on [tumblr](http://jhoomwrites.tumblr.com)

Alone in the corner on the second floor of their dorm is a four person suite, nestled between a community kitchen and a study lounge.  It’s perfectly situated for four boys who get up to no good.  Which is exactly why Dean, Cas, Jimmy, and Benny love it.  They can sneak in their ill gotten alcohol and drink without the RA’s breathing down their backs.  They can play music louder than anyone else because there’s no one around to bother.

And apparently they can get themselves into the most ridiculous bet any of them has ever thought up.

Sophomore year starts with them making great use of their relative privacy and enjoying themselves immensely.  Benny’s even almost a little bummed when he disappears a few weeks into the fall semester to do his study abroad in France.

… So really, this whole mess is Benny’s fault for leaving them alone.

It’s a regular, boring old Thursday night.  The twins are sprawled across their beds while Dean sits in between on their ridiculously oversized beanbag chair, all three engrossed with the latest episode of Doctor Sexy.  Well, that’s not completely true.  Cas is politely staying quiet and working on some homework while the other two watch.  But he _does_ comment from time to time.  

Halfway through the episode, it’s revealed that one of the doctors has a panty thing.  The guy gets injured and rushed in for emergency surgery.  When they start cutting off his clothes, they find a satiny pink pair of panties, complete with a baby blue bow, on him.  Cue the show making a big deal out of it, the other hospital staff completely scandalized that the butch Dr. Cassidy could possibly enjoy such a kink.  

“Pssh, what’s the big deal?” Dean grumbles as he balls up a piece of paper and throws it at the tv as a commercial break starts.  “They’re just panties.”

“Have you ever worn panties, Dean?” Castiel asks, proving that he is in fact paying attention.

Dean blushes before stuttering out, “Well, no-”

“Then how can you say it’s not a big deal?” Jimmy challenges.

“Uh, because it’s just underwear?  The only reason it’s even remotely weird in the show is because they found out.  I bet no one would even _know_ if I started wearing panties.  People do all sorts of weird shit and it’s no big deal unless people make it one.”

“Maybe,” Cas agrees.  He closes his textbook and scoots to the edge of his bed.  “But it takes a certain amount of confidence and self-assurance to be able to wear panties and not let it get to you.  To worry about your shirt riding up or your pants slipping down or having to… _adjust_.”

“Wh-what?” he stutters.  

Jimmy jumps in with a huge smile to piggyback on his brother’s comments.  “No, Cas is right!  No way you could pull it off, Winchester.  You’re all talk!  You’d be jumpy as shit all day, terrified someone would find out!”

(Maybe somewhere in the back of his mind, Jimmy hoped that Dean would smugly stand up and reveal that he’s _currently_ wearing panties.  Alas, that doesn’t happen.)

“Pssh, you’re all up on my case about this as though you could do better.  I bet I could last way longer than either of you.”

“Uh, no way!” Jimmy laughs out.  “I’ve seen the comically loose boxers you and Cas both wear.  You wouldn’t know what to do with underwear that actually cradles your junk.  You wouldn’t last a whole day.”

Cas rolls his eyes.  “And we both know you’re no better equipped to do better.  You’d probably freak out.  You’ve been allergic to pink and anything even remotely pastel ever since the Easter bunny incident when we were five.”

(Dean flashes Cas raised eyebrows that’s all question marks.  Cas returns it with a look that assures him he’ll fill Dean in on it later.  The other boy nods and gives a small thumbs up.)

Ignoring both of them, Jimmy practically shouts, “They come in other colors!”  Then his voice wavers a bit.  “... Right?”

“Dude thinks he can handle panties when he can’t even deal with wearing pastels?”  Dean chuckles while shaking his head in disbelief.

After a few more minutes of arguing, the boys settle on a bet.  The terms are simple enough.  Whoever can go the longest wearing only panties - no boxers, no briefs, no boxer briefs, no going commando, none of it - wins.  As they each angrily grab their laptops to begin ordering the necessary panty provisions, Doctor Sexy all but forgotten, new rules starting springing up.

“There should be a rule that you gotta have at least one pair with a bow.”

“And lace.”

“Bikini cut?  Cheekies?  I don’t know what those are but we gotta have a rule about ‘em.”

“But can we at least agree on no thongs?”

“Thongs it is!”

There’s a lot of angry clicking as they try to find the perfect pairs to help them win the bet.  Dean’s reading the sizing charts when Cas coughs to get their attention.  “How are we going to… check?  To make sure everyone’s following the rules?”

After a bit of arguing, they agree that all of their non-panty underwear will be on lockdown in Benny’s empty trunk (and thank god Benny’s not there for them to have to explain that one).  They also decide to show a peek of their panties each morning and evening, plus any other time one of the others asks.  

“The only stipulation is that it can’t be in public.  Do it in the bathroom or something.”

“Riiight, because showing a guy your panties in public is waaay gayer than going to the bathroom to do it.”

“Hey, if you wanna show the whole campus your goods, you go for it, Jimbo.”

“No no, in private works for me.”

When their digital carts full, Jimmy’s about to hit the ‘checkout button’ when he stops and eyes the other two suspiciously.  “Wait…  What does the winner get?”

Cas and Dean visibly start at that.  They’d been so preoccupied with the bet itself and their purchases that they didn’t even think ahead that far.

“Uh… bragging rights?” Dean suggests.

Jimmy’s quick to shake his head.  “Nuh uh, not good enough.  If I gotta wear panties for a month or whatever, I want something more than being able to _say_ I wore panties for a month and did it better than my roommates.”

“Well you got any suggestions?”

“Blackmail,” Cas says simply.  “Every morning when we do the first check of the day, we take pictures.  The winner gets to keep all of the photos and do whatever he wants with them.”

“Sounds good to me.”  (Dean very carefully refrains from pointing out that such blackmail is useless for the twins.  No one would ever be able to tell the difference between them in pictures, but hey, he’s not about to make this negotiation any harder.)

After a moment’s hesitation, Jimmy agrees.  They shake on it and happily continue shopping.

\- - - -

Things start off innocently enough.  Their respective packages arrive in discreet (read: boring) brown packages within a couple days of each other.  Once they arrive, they lock up all their underwear, give the key to their friend Garth for safe-keeping, and get started.  

As one could well imagine, three teenage boys with piles and piles of panties are ridiculous.  Despite all of their earlier bravado, all of them start to lose their nerve when it comes to picking the first pair.  And then it’s picture them and they definitely reconsider if this is worth it.  But none of them want to be the first to chicken out, so they grimace and get on with it.

A couple days in, though, and that shyness fades away.  Their camera poses get cheesier and cheesier.  Dean likes to flex his muscles and give them his best Blue Steel.  Jimmy likes to mimic Playboy pin-ups, complete with his best ‘come fuck me’ eyes.  Castiel’s stern, unperturbed look as he confidently shows off his *ahem* _assets_ makes Dean (and admittedly Jimmy) a little hot under the collar.  

They’re clearly comfortable wearing the panties, so if they want to actually _win_ , they have to make the others decidedly _un_ comfortable.  Trash talking is the obvious next step.  

“Don’t you like pretty in those.  You should probably do yourself a favor and drop outta school, get a job as an underwear modal or a stripper.”

“Ain’t that a pretty picture.  Wonder how many hits I could get on a porn blog, postin’ these pics of your ass.”

“No wonder you were so sure of yourself when we made the bet.  You look like you’ve been wearing these your whole life.”

All in good fun of course.  The most they can get is a blush out of the others, but no weakening of their resolve.  

But then the _incidents_ start happening.

It’s about a week in and they’ve gotten used to not only wearing panties, but _seeing_ each other wearing panties.  So one morning when Dean comes out of the shower with his green polka dotted pair, Jimmy thinks nothing of it.  He also thinks nothing of it when he notices that the material’s bunched up on one side, the hem not laying flat along the curve of Dean’s ass, to go over and _fix_ it for him.  With sure hands, he smooths out the material.  As if to cover up how awkward the moment is, he spanks Dean’s ass and pushes him to his dresser.

Dean puts on his pants in record time after that, unless other _fit_ issues become obvious.

And a couple days later, Dean may or may not get an eyeful of the twins wearing _matching_ panties.  And perhaps, for two seconds there when he can’t tell them apart, his heart starts racing in a not unpleasant way.  For a second he even wonders _how_ identical the twins are.  Surely his eyes don’t drop to their crotches, seeing if the bulges there are an indication as to who’s who.  

~~He most definitely does _not_ then wonder if they’d feel different in his hands or taste different on his tongue.~~

Let’s just say, it confuses Dean on a number of levels.  

The very next day, Castiel’s working on his computer when he sees Jimmy puttering around the room.  There’s something off about it, so he slams his book down and stands up.  

“Panty check.”  Jimmy raises an eyebrow in question at him.  “You look too comfortable.  It’s suspicious.”

And because Jimmy’s a little shit, he puts his hands up in the air.  “You’re welcome to come and check.”  

Cas sighs in exasperation.  “Can’t you just pull your pants down to show me?  Why must you make this difficult?”

“Hey, if you wanna check, come check.  I don’t have to make it _easy_ for you.”

He feels as though Jimmy’s trying to call his bluff, so he storms over with a determined look in his eyes.  Jimmy keeps his arms up and out of the way as Castiel moves into his personal space.  He holds Jimmy’s gaze as his hands work his buckle and then the zipper of his fly.  By then they’re both breathing a little heavier, but Cas doesn’t stop.  

Instead of pulling the pants aside, Cas wiggles them down enough that they fall loose around Jimmy’s ankles.  Only then does he look down to inspect his brother.

A pair of navy, silk panties are starting to strain under the weight of Jimmy’s growing erection.  He doesn’t know why he does it, but Castiel reaches out to trace the line of silk at the waistband.  Jimmy shudders and gulps in response, but doesn’t protest or step away.  It’d be so easy, he thinks, to step forward and align their cocks - Jimmy’s in the dark silk, Cas’ behind the thin layer of lace and the rough denim   So _so_ easy-

When they hear a key in the lock, they jump apart.  Castiel takes a few steps back while Jimmy scrambles to pull his pants back on.  

Dean seems to sense some of the remaining tension in the air because he freezes in the doorway and looks between the two.  Jimmy’s nonchalance doesn’t even seem forced when he rolls his eyes, “This loser’s still making me do panty checks.”

Everything spirals out of control soon after that.

Jimmy’s out at class and Cas is his usual I-haven’t-had-caffeine-yet self.  As Dean heads to the shower, he pokes at the lump and warns Cas to get up.  Castiel is, of course, exactly where Dean left him when he comes out of the bathroom twenty minutes later.  

For some reason, he gets it in his head exactly how he can wake up his roommate.  So he smiles coyly at Castiel as he walks to his dresser.  “Hey Cas, can you help me with something?”

Cas grumbles something unintelligible from where he’s hiding beneath his comforter.  

“It’s just… I could really use some help picking out what panties I should wear today and I thought-”

The other boy springs out of bed, one eye still closed as the other blinks away sleep, and stalks over to the dresser.  Dean tries not to laugh at how adorable it is, especially because morning Cas is a scary Cas, and stands aside as Castiel pulls open the top drawer and starts sorting through the various pairs.  

Finally he settles on a vibrant green.  He holds it up to Dean’s eyes first, the material almost caressing his cheek before Castiel’s shoving it into his chest.  “These ones.”

Dean accepts them and starts shuffling away, only to find Cas on his heels.  “What’re you doing, man?”

“I picked them.  I want to see you put them on.”

His mouth goes dry and there’s a surprising amount of blood rushing south, but Dean nods and steps out of his towel.  He’s blushing from the roots of his hair down his chest, but Castiel’s not looking anywhere below his waist.  But he refuses to let Cas intimidate him, puffing up his chest a bit as he carefully steps into the panties Cas picked out for him.

_~~**Fuck** Cas picked out his panties and is watching him put them on.  Don’t get hard don’t get hard don’t get hard~~- _

Right as he’s pulling the soft material up his thighs, Cas’ hands take over and pull them the rest of the way up.  Once he’s set them on Dean’s hips, the son of a bitch snaps the waistband and then _adjusts_ Dean’s cock like it’s the most normal thing in the world.  Then he winks at Dean and disappears into the bathroom for his own shower.

In the cold that fills in the empty space Cas left behind, Dean wonders how long they can keep up this secondary game they seem to be playing before someone cracks.  

Turns out not that long.

Castiel ditches his club meetings that day because he’s hard since the whole thing with Dean that morning.  How pretty the older boy had looked, flushed but open to Castiel’s touch…  He already jerked off in the shower, but it does nothing to cool his arousal once Jimmy sends him a snapchat of him and Dean showing off their panties for the day with a little not that says _i’m jealous u didn’t pick mine 2_.

Quite honestly this is the most sexually frustrating bet he could’ve ever made with anyone ever.  

Both Dean and Jimmy should be in class right now, so Castiel hopes he’ll have a good amount of alone time to enjoy himself and try to get a handle on his feelings.  Because being attracted to Dean is nothing knew.  Hell, being attracted to _Jimmy_ isn’t entirely out of the blue.  It’s the _urgency_ behind it that’s now driving him mad.

He opens the door to their dorm room and yeah scratch that, it’s not this ridiculous bet or the unresolved sexual tension that’s going to kill him.  It’s the image before him right now.

Jimmy’s lying on his back wearing nothing but the cream colored panties he’d so boldly shown off in his picture.  Which alone would be enough to give Cas pause.  Right now, though, he’s more focused on the dick in Jimmy’s mouth.  And the dick in Dean’s mouth as the two enthusiastically blow each other, panties pushed aside barely enough to free their cocks for the other’s enjoyment.

Slowly, he closes the door behind him.  As the lock clicks into place, Jimmy and Dean both moan.  Their eyes are on Castiel as he approaches the bed.  He kicks off his shoes and socks before tossing his shirt and jeans aside, all while deciding where he’d rather start.

Given that Dean’s on top, it seems simplest to crawl onto the bed behind him.  While Jimmy and Dean continue to blow each other, Castiel nudges Dean’s legs apart before pulling the fabric taut to reveal his hole.  He teases him with his fingers for a moment, gentle caresses that make him buck and groan (which in turn make Jimmy buck and groan).  

When he dips down to kiss the puckered muscle before giving a tentative lick, the sounds Dean makes are music to his ears.

By the time he’s working his tongue inside, Dean’s enthusiastically thrusting back onto his tongue and forwards into Jimmy’s mouth.  Somehow he manages to keep bobbing up and down, and Castiel occasionally whispers praise to him.

“Good boy.  You make Jimmy come for me, alright?  Doing such a good job for us…”

Castiel’s more than satisfied to help bring Dean and Jimmy to orgasm, to enjoy their desperate moans.  But then he feels a hand working down the waistband of his thong, easing them down his legs before nimble fingers start massaging his balls and working his shaft.  He pulls away from Dean only long enough to see his brother’s hands around his cock.

They soon lose all finesse, merely trying to get each other off and stave off their own orgasms until the others have finished.  Dean comes first, hole clenching around Cas’ tongue and then he’s jerking away when he becomes too sensitive.  Jimmy licks him clean but otherwise lets him pull away as he flops onto his side, eyes hooded but intent to watch the other two.  

After a nudge forward, Castiel takes Dean’s place.  He hesitates a second before he swallows Jimmy down.  Jimmy guides Cas’ cock to his mouth, licking tentatively before doing the same.  They work in tandem so seamlessly that it doesn’t look like it’s their first time blowing each other.

“Oh _fuck_ ,” Dean hisses.  “Not fair… Why you gotta make me watch this after I’ve already come?”

Cas falls apart at that, the sudden realization hits him of _what_ he’s doing and _who_ he’s doing it with and _who’s_ watching them.  As soon as his twin’s come hits his mouth, Jimmy spasms and fills Castiel’s mouth.  They suck each other dry, milk the last remaining drops before they break off and collapse in a heap.  Dean reaches in and manhandles Cas so that he’s not squashing his brother, then wraps his arms around Castiel and his legs around Jimmy.

“That was fun,” he mumbles.  

“Mmhmm,” the twins agree in unison.  

“We should do it again sometime.”

“Gimme a few hours and I’ll be ready to go again,” Jimmy grunts around a yawn.  Snores fill the air a moment later, tickling their feet.

In the end, they decide to call it a draw.  The thrill of the bet has lost its edge, replaced instead by the thrill of their new relationship.  Not to say that they don’t still wear their panties occasionally (read: often), but it’s mostly to rile each other up.

~~Poor Benny though when he returns from his trip.  If he thought the twins lowkey flirting with Dean _before_ all this was bad, he’s in for a rude awakening.~~

**Author's Note:**

> **Bonus: Cut Scene**
> 
> Dean storms into the room and throws his backpack down in frustration. The twins don’t comment, just look at him expectantly and wait for the tirade that will inevitably follow such a display. “How am I supposed to go on dates and get laid when we got this bet going on, huh?”
> 
> “Who exactly are you trying to date?” Jimmy demands. His tone is borderline angry and accusatory, but mostly it just comes across as inquisitive. … He hopes.
> 
> “Lisa Braden,” he says, as if it’s obvious.
> 
> “What’s wrong Dean?” Castiel asks, and it bugs Jimmy for some reason that this whole thing doesn’t seem to bother his brother at all. “No longer comfortable in your masculinity?”
> 
> Jumping on, Jimmy adds, “Don’t like the satin anymore? And who knew baby blue is your color.”
> 
> The other boy rubs his hand over his face like he’s bracing himself. Finally, he grits out, “Okay, look… Maybe I’m only saying this because it’s you two, but you know damn well they feel amazing. I just… I don’t like being judged for somethin’ by someone who barely knows me, you know? I don’t like worrying that something as innocuous as the type of underwear I have on could be a dealbreaker.”
> 
> The twins share a look and then shrug.
> 
> “What? That’s it? You guys just shrug at me? Thanks for the help.”
> 
> “Well,” Castiel says carefully, “Unless you date someone else in this room, I don’t know what possible solution there is.”  
> They’re all pretty quiet after that.


End file.
